JP2003523331A - 官能基が付与されたβ−（１，３）−グルカン誘導体の調製方法 - Google Patents

官能基が付与されたβ−（１，３）−グルカン誘導体の調製方法

Info

Publication number: JP2003523331A
Authority: JP; Japan
Prior art keywords: group; glycosyl; carbon atoms; formula; benzyl
Prior art date: 2000-02-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2001557884A

Other languages

English (en)

Japanese (ja)

Inventor

ジャン−クロード・イヴァン

フラン・ジャモワ

ヴァンサン・フェリエール

ダニエル・プルスクレック

Original Assignee

ラボラトワールゴエマール

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-02-04

Filing date

2001-02-02

Publication date

2003-08-05

2001-02-02 Application filed by ラボラトワールゴエマール filed Critical ラボラトワールゴエマール

2003-08-05 Publication of JP2003523331A publication Critical patent/JP2003523331A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 42
125000000524 functional group Chemical group 0.000 title claims abstract description 17
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical class OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 title claims abstract description 8
-1 sulfate ester Chemical class 0.000 claims abstract description 62
150000001875 compounds Chemical class 0.000 claims abstract description 51
239000000937 glycosyl acceptor Substances 0.000 claims abstract description 36
239000000348 glycosyl donor Substances 0.000 claims abstract description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 58
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 41
239000000126 substance Substances 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
125000003147 glycosyl group Chemical group 0.000 claims description 28
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 9
125000002976 glycerolipid group Chemical group 0.000 claims description 9
125000002328 sterol group Chemical group 0.000 claims description 9
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 9
125000005039 triarylmethyl group Chemical group 0.000 claims description 9
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 8
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125000004803 chlorobenzyl group Chemical group 0.000 claims description 8
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125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
125000005425 toluyl group Chemical group 0.000 claims description 5
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
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238000003786 synthesis reaction Methods 0.000 description 31
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LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 7
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239000002243 precursor Substances 0.000 description 7
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STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 7
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
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NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 3
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000013519 translation Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/08—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium
- C07H5/10—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium to sulfur
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Crystallography & Structural Chemistry (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Steroid Compounds (AREA)
Cosmetics (AREA)

JP2001557884A 2000-02-04 2001-02-02 官能基が付与されたβ−（１，３）−グルカン誘導体の調製方法 Pending JP2003523331A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR0001429A FR2804684B1 (fr)	2000-02-04	2000-02-04	Procede pour la preparation de derives fonctionnalises de beta-(1,3)-glucanes
FR00/01429		2000-02-04
PCT/FR2001/000329 WO2001057053A1 (fr)	2000-02-04	2001-02-02	PROCEDE POUR LA PREPARATION DE DERIVES FONCTIONNALISES DE β-(1,3)-GLUCANES

Publications (1)

Publication Number	Publication Date
JP2003523331A true JP2003523331A (ja)	2003-08-05

Family

ID=8846670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2001557884A Pending JP2003523331A (ja)	2000-02-04	2001-02-02	官能基が付与されたβ−（１，３）−グルカン誘導体の調製方法

Country Status (11)

Country	Link
US (1)	US6951934B2 (de)
EP (1)	EP1252171B1 (de)
JP (1)	JP2003523331A (de)
AT (1)	ATE370155T1 (de)
AU (1)	AU2001231973A1 (de)
CA (1)	CA2399161C (de)
DE (1)	DE60129929T2 (de)
ES (1)	ES2292557T3 (de)
FR (1)	FR2804684B1 (de)
PT (1)	PT1252171E (de)
WO (1)	WO2001057053A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050065114A1 (en) *	2003-09-23	2005-03-24	Jean-Claude Yvin	Therapeutical treatment with oligo-beta- (1,3) -glucans, drugs used in said treatment
US7070778B2 (en)	2003-10-30	2006-07-04	Laboratoire Goemar Sa	Therapeutical combination against cancer
FR2910322B1 (fr) *	2006-12-22	2009-10-30	Mer Soc Par Actions Simplifiee	Utilisation d'oligo-b-(1,3)-glucanes modifies pour le traite traitement de maladies du systeme immunitaire, oligo-b-(1,3) glucane-(1,3)-mannose, oligo-b-(1,3)-glucane-(1,3)-mannitol et leurs derives, ...
US20100076239A1 (en) *	2007-09-07	2010-03-25	University Of South Florida	Asymmetric cyclopropanation of electron-deficient olefins with diazo reagents
EP2920193A4 (de) *	2012-11-16	2016-09-14	Univ Arizona State	Synthese von tensiden auf der basis von kohlehydraten

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR860379B (en) *	1985-02-22	1986-06-11	Akzo Nv	Novel disaccharide and trisaccharide derivatives of the lipid a type
US5721368A (en) *	1996-07-22	1998-02-24	Merck & Co. Inc.	Process for synthesizing carbapenem side chain intermediates
FR2777281B1 (fr) *	1998-04-14	2000-06-30	Goemar Lab Sa	Procede de synthese du d-laminaribiose

2000
- 2000-02-04 FR FR0001429A patent/FR2804684B1/fr not_active Expired - Fee Related
2001
- 2001-02-02 ES ES01904046T patent/ES2292557T3/es not_active Expired - Lifetime
- 2001-02-02 AT AT01904046T patent/ATE370155T1/de not_active IP Right Cessation
- 2001-02-02 DE DE60129929T patent/DE60129929T2/de not_active Expired - Lifetime
- 2001-02-02 WO PCT/FR2001/000329 patent/WO2001057053A1/fr not_active Ceased
- 2001-02-02 JP JP2001557884A patent/JP2003523331A/ja active Pending
- 2001-02-02 EP EP01904046A patent/EP1252171B1/de not_active Expired - Lifetime
- 2001-02-02 CA CA2399161A patent/CA2399161C/en not_active Expired - Fee Related
- 2001-02-02 US US10/182,976 patent/US6951934B2/en not_active Expired - Fee Related
- 2001-02-02 AU AU2001231973A patent/AU2001231973A1/en not_active Abandoned
- 2001-02-02 PT PT01904046T patent/PT1252171E/pt unknown

Also Published As

Publication number	Publication date
ATE370155T1 (de)	2007-09-15
DE60129929T2 (de)	2008-04-30
US6951934B2 (en)	2005-10-04
CA2399161A1 (en)	2001-08-09
PT1252171E (pt)	2007-11-15
FR2804684B1 (fr)	2002-06-28
FR2804684A1 (fr)	2001-08-10
US20030045706A1 (en)	2003-03-06
WO2001057053A1 (fr)	2001-08-09
DE60129929D1 (de)	2007-09-27
EP1252171A1 (de)	2002-10-30
AU2001231973A1 (en)	2001-08-14
CA2399161C (en)	2010-10-12
ES2292557T3 (es)	2008-03-16
EP1252171B1 (de)	2007-08-15

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